Phosgene → L-Glutamic acid, 5-(phenylmethyl) ester

HRID 874081

反応式

HRID 874081 の反応式
O[NH:2][C@H:3]([C:16](N)=[O:17])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(Cl)(Cl)=[O:20]>C1COCC1>[NH2:2][C@H:3]([C:16]([OH:17])=[O:20])[CH2:4][CH2:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

4

反応物 2

HCID 6371PhosgeneHCID 131732571HO-Glu(Bzl)-NH2

生成物 1

HCID 122337L-Glutamic acid, 5-(phenylmethyl) ester収率 99.7%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

HO-Glu(Bzl)-NH2 (30.0 g, 126.0 mmol) was suspended in 300 mL of anhydrous THF and heated to 50° C. Phosgene (20% in toluene) (81.3 mL, 164.6 mmol) was added to the amino acid suspension by syringe, and the amino acid dissolved over the course of approx. 30 minutes, forming a clear solution. The solution was concentrated by rotory evaporation, dissolved in ˜150 mL of anhydrous THF, and transferred to an Erlenmeyer flask. Hexane was added and the product was allowed to crystallize overnight. The NCA was isolated by filtration and dried in vacuo. 29.8 g (90% yield) of Glu(Bzl) NCA was isolated as a white, crystalline solid. 1H NMR (CDCl3) δ 7.36 (5H), 6.22 (1H), 5.14 (2H), 4.35 (1H), 2.61 (2H), 2.29 (1H), 2.14 (1H) ppm.

後処理

  1. customforming a clear solution
  2. concentrationThe solution was concentrated by rotory evaporation
  3. dissolutiondissolved in ˜150 mL of anhydrous THF
  4. additionHexane was added
  5. customto crystallize overnight
  6. customThe NCA was isolated by filtration
  7. customdried in vacuo

出典と根拠

ORDレコード
ord-7b8561a1c8dd467aa7304fb2998c6784
出典データセット
uspto-grants-2015_03
特許番号
US08980326B2

関連ノート

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